US3488180A - Gilsonite salts of herbicidal acid and plant hormone type acids - Google Patents
Gilsonite salts of herbicidal acid and plant hormone type acids Download PDFInfo
- Publication number
- US3488180A US3488180A US456563A US3488180DA US3488180A US 3488180 A US3488180 A US 3488180A US 456563 A US456563 A US 456563A US 3488180D A US3488180D A US 3488180DA US 3488180 A US3488180 A US 3488180A
- Authority
- US
- United States
- Prior art keywords
- gilsonite
- acid
- salts
- acids
- herbicidal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title description 31
- 150000003839 salts Chemical class 0.000 title description 31
- 230000002363 herbicidal effect Effects 0.000 title description 22
- 150000007513 acids Chemical class 0.000 title description 16
- 239000003375 plant hormone Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 description 20
- 239000004009 herbicide Substances 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910017464 nitrogen compound Inorganic materials 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- -1 heterocyclic nitrogen compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000007670 refining Methods 0.000 description 7
- 150000002830 nitrogen compounds Chemical class 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 2
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012633 leachable Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 2
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- PTFNNDHASFGWFI-UHFFFAOYSA-N 2,4,5-trichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C=C1Cl PTFNNDHASFGWFI-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 101100456571 Mus musculus Med12 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- LUUJSGOVJSIWFL-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O.CC(C)=O LUUJSGOVJSIWFL-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
Definitions
- This invention relates to a novel class of economical herbicides and more particularly to herbicides comprising the reaction product of heterocyclic nitrogen compounds derived from gilsonite with acids selected from the group consisting of herbicidal acids and plant hormone-type acids to give salts which are desirably nonvolatile. Also, these salts will not leach out and they are oil soluble, which is preferred for plant Work. They are useful for either pre-emergence or post-emergence control of plants.
- An object of the invention herein is to provide such an improved herbicide.
- Another object is to provide a low-cost herbicide.
- Still another object is to provide a herbicide which is substantially non-volatile.
- a further object is to provide a herbicide Which is substantially non-leachable.
- a still further object is to provide a herbicide which by reason of its non-volatility and non-leachability, is extremely selective.
- Another object is to provide a herbicide which is longacting.
- the herbicidal salts produced by this invention are substantially inexpensive. This is in contrast to most amine salt herbicides which are expensive. The reason is that the gilsonite components of the salts are very inexpensive and therefore greatly reduced the cost thereof.
- the gilsonite component of the salts of the invention occurs as a by-product in the manufacture by The American Gilsonite Company of petroleum products from the ice mineral gilsonite, The company describes it as a material containing predominantly mixed alkylated pyridines, pyrroles, indoles, and quinolines, with some of the substituent carbon chains being olefinic. It also contains some unidentified non-nitrogenous material. However, it is believed to be an inordinately complex mixture of chemical structures. Well over one-hundred dilferent compounds are indicated as being present in the mixture, based on gas chromatigraphic procedures. The extreme complexity of such a mixture of materials renders a complete qualitative analysis almost prohibitive.
- the salts of this invention utilization of all crude, semi-purified by-products and having a boiling point of greater than about 200 F. resulting from the refining of gilsonite, are utilizable.
- the composition of such mixed heterocyclic nitrogenous by-products will vary with the composition of the original gilsonite, the point in the refining process from which they are extracted, the boiling range in which they are extracted and the like.
- the invention herein described presupposes utilization of all such mixed heterocyclic nitrogenous compounds either in crude or in purified forms; however, the preferred mixed heterocyclic nitrogen compounds in the practice of this invention are those which have a boiling range of about 200 F. to about 750 F. and particularly those which have an average boiling point within the range of about 450 to about 750 F.
- the invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound, and the composition of matter possessing the characteristics, properties, and the relation of constituents which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
- the salt formed will test as follows for herbicidal activity (pro-emergence treatment):
- EXAMPLE IV The gilsonite monosalt of Endothal (3,6-endoxohydro phthalic acid) is prepared by admixing one molecular equivalent of gilsonite with the endothal-l, dissolved in benzene, and then heating to complete the reaction.
- Table 3 illustrates field results that are obtainable using this salt:
- the gilsonite disalt of Endothal is prepared by admixing a neutral equivalent weight of gilsonite with 3,6-endoxohydrophthalic acid (the anhydride may also be used) dissolved in petroleum ether and then heating the mixture until the reaction is complete,
- a water emulsifiable salt of the herbicide of Example I may be made by dissolving it in a SO-SO-mixture of isopropanol-diacetone solvent with 10-15% cationic Ethomeen (ethoxylated amine) as an emulsifier.
- EXAMPLE VII The 2,4,5-T gilsonite salt of Example II is best dissolved in diacetone with 1015% Ethomeen 8/25 (ethoxylated (15 moles) amine) as an emulsifier.
- herbicidal acids and plant hormonetype acids there is contemplated any acid which has herbicidal activity, such as, for example:
- gilosonite to each carboxylic group in the acid is employed to make the salt. Mixtures of the acids may also be used.
- a solvent is preferably used, and this may be any polar or non-polar solvent such as, for example: isopropanol, methanol, acetone, diacetone, xylene, aromatic naphthalenes, and all the petroleum distillates.
- Heat is also preferably utilized to speed up the reaction.
- herbicidal salts of the invention for plant growth control, 0.25 to 10 pounds (lb.) per acre are utilized dependent upon the plant(s) being controlled and the particular salt(s) employed. Mixtures of the salts may also be used.
- the salt is first dissolved in the desired solvent, such as indicated in the preceding paragraph, then an appropriate emulsifier of the anionic, cationic, or nonionic type is added and the product emulsified in water to the desired spray concentration.
- a method for the preparation of gilsonite salts comprising reacting a mixture of heterocyclic nitrogen compounds as contained in the crude, semi-purified or purified by-products having a boiling point of about 200 F. to 750 F. resulting from refining of gilsonite with an acid selected from the group consisting of herbicidal acids and plant hormone-type acids to form the salt, said reaction being carried out using a reaction solvent and heat.
- a method for the preparation of the gilsonite salt of 3,6-endoxohydrophthalic acid comprising reacting a neutral equivalent amount of a mixture of heterocyclic nitrogen compounds as contained in the crude, semipurified or purified by-products having a boiling point of about 200 F. to 750 F. resulting from refining of gilsonite with said acid in the presence of a solvent and heat.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45656365A | 1965-05-17 | 1965-05-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3488180A true US3488180A (en) | 1970-01-06 |
Family
ID=23813259
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US456563A Expired - Lifetime US3488180A (en) | 1965-05-17 | 1965-05-17 | Gilsonite salts of herbicidal acid and plant hormone type acids |
Country Status (3)
Country | Link |
---|---|
US (1) | US3488180A (pm) |
GB (1) | GB1118424A (pm) |
NL (1) | NL6606793A (pm) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3246015A (en) * | 1961-11-24 | 1966-04-12 | Pennsalt Chemicals Corp | Tertiary amine salts of 3, 6-endoxohydro-orthophthalic acids |
-
1965
- 1965-05-17 US US456563A patent/US3488180A/en not_active Expired - Lifetime
-
1966
- 1966-05-17 GB GB21943/66A patent/GB1118424A/en not_active Expired
- 1966-05-17 NL NL6606793A patent/NL6606793A/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3246015A (en) * | 1961-11-24 | 1966-04-12 | Pennsalt Chemicals Corp | Tertiary amine salts of 3, 6-endoxohydro-orthophthalic acids |
Also Published As
Publication number | Publication date |
---|---|
GB1118424A (en) | 1968-07-03 |
NL6606793A (pm) | 1966-11-18 |
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